EP1160237A3 - Method for the preparation of optically active trimethyllactic acid and its esters - Google Patents

Method for the preparation of optically active trimethyllactic acid and its esters Download PDF

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Publication number
EP1160237A3
EP1160237A3 EP01111927A EP01111927A EP1160237A3 EP 1160237 A3 EP1160237 A3 EP 1160237A3 EP 01111927 A EP01111927 A EP 01111927A EP 01111927 A EP01111927 A EP 01111927A EP 1160237 A3 EP1160237 A3 EP 1160237A3
Authority
EP
European Patent Office
Prior art keywords
esters
optically active
preparation
acid
trimethyllactic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01111927A
Other languages
German (de)
French (fr)
Other versions
EP1160237A2 (en
Inventor
Wolfram Dr. Sirges
Claus Dr. Dreisbach
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Chemicals AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1160237A2 publication Critical patent/EP1160237A2/en
Publication of EP1160237A3 publication Critical patent/EP1160237A3/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form

Abstract

Die Erfindung betrifft ein neues Verfahren zur Herstellung optisch aktiver Trimethylmilchsäure und/oder ihrer Ester durch katalytische Hydrierung von Trimethylbrenztraubensäure und/oder ihrer Ester in Gegenwart von Edelmetallkomplexkatalysatoren mit Phosphor-haltigen Liganden.The invention relates to a new method for producing optically active Trimethyllactic acid and / or its esters by catalytic hydrogenation of Trimethylpyruvic acid and / or its esters in the presence of noble metal complex catalysts with phosphorus-containing ligands.

EP01111927A 2000-05-31 2001-05-18 Method for the preparation of optically active trimethyllactic acid and its esters Withdrawn EP1160237A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10027154A DE10027154A1 (en) 2000-05-31 2000-05-31 Process for the production of optically active trimethyllactic acid and its esters
DE10027154 2000-05-31

Publications (2)

Publication Number Publication Date
EP1160237A2 EP1160237A2 (en) 2001-12-05
EP1160237A3 true EP1160237A3 (en) 2003-11-12

Family

ID=7644334

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01111927A Withdrawn EP1160237A3 (en) 2000-05-31 2001-05-18 Method for the preparation of optically active trimethyllactic acid and its esters

Country Status (4)

Country Link
US (1) US6583312B2 (en)
EP (1) EP1160237A3 (en)
JP (1) JP2002003441A (en)
DE (1) DE10027154A1 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1610688A (en) * 2000-11-17 2005-04-27 宾夕法尼亚州研究基金会 Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions
CA2524915A1 (en) * 2003-05-09 2004-11-18 Solvias Ag Phospholane salts and their use in enantioselective hydrogenation
WO2004111063A2 (en) * 2003-06-13 2004-12-23 Lanxess Deutschland Gmbh Chiral ligands for application in asymmetric syntheses
JP4519500B2 (en) * 2004-03-30 2010-08-04 高砂香料工業株式会社 Method for producing neutral rhodium-phosphine complex
JP2008088153A (en) * 2006-04-10 2008-04-17 Okayama Univ Method for producing amide compound and catalyst used for the same method
CN102112887B (en) * 2008-06-03 2015-06-10 泰拉丁公司 Processing storage devices
EA027889B1 (en) * 2010-09-10 2017-09-29 Каната Кемикал Текнолоджиз Инк. Biaryl diphosphine ligands, intermediates of the same and their use in asymmetric catalysis
CN103204877A (en) * 2012-01-11 2013-07-17 中国科学院大连化学物理研究所 Electron-deficient axially-chiral diphosphine ligands, and preparation method thereof
JP6455893B2 (en) 2013-03-11 2019-01-23 ラトガース，ザ ステート ユニバーシティ オブ ニュー ジャージー Organometallic catalysis for asymmetric transformations
CN112457182A (en) * 2020-12-16 2021-03-09 江苏慧聚药业有限公司 Preparation method of flurbiprofen impurity

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0295890A2 (en) * 1987-06-19 1988-12-21 Takasago International Corporation Process of preparing optically active alcohol
US5198569A (en) * 1990-11-02 1993-03-30 Ciba-Geigy Corporation Process for the preparation of optically active aliphatic hydroxycarboxylic acids
EP0643065A1 (en) * 1993-09-10 1995-03-15 Bayer Ag Novel bisphosphines for asymetric hydrogenation catalysts
EP0901997A1 (en) * 1997-09-05 1999-03-17 Takasago International Corporation Process for producing optically active alcohol compound
EP0965574A2 (en) * 1998-06-19 1999-12-22 Degussa-Hüls Aktiengesellschaft Process for enantioselective hydrogenation

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK350383A (en) 1982-08-27 1984-02-28 Hoffmann La Roche phosphorus compounds
JPS6163690A (en) 1984-09-04 1986-04-01 Takasago Corp Ruthenium-phosphine complex
JPS62265293A (en) 1986-05-13 1987-11-18 Takasago Corp Ruthenium-phosphine complex
JPS6341487A (en) 1986-08-06 1988-02-22 Takasago Corp Ruthenium-phosphin complex
JPH0757758B2 (en) 1988-10-24 1995-06-21 高砂香料工業株式会社 Ruthenium-phosphine complex
DK0398132T3 (en) 1989-05-18 1995-12-18 Hoffmann La Roche phosphorus compounds
JP2775335B2 (en) 1990-08-01 1998-07-16 高砂香料工業株式会社 Ruthenium-phosphine complex and its production intermediate
US5436067A (en) 1993-11-22 1995-07-25 Kuraray Chemical Co., Ltd. Freshness keeping sheet
DE19522293A1 (en) 1995-06-20 1997-01-02 Bayer Ag New bisphospins as catalysts for asymmetric reactions
EP0967015B1 (en) 1998-06-19 2005-01-12 Degussa AG Use of ferrocenyl ligands in catalytic enantioselective hydrogenation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0295890A2 (en) * 1987-06-19 1988-12-21 Takasago International Corporation Process of preparing optically active alcohol
US5198569A (en) * 1990-11-02 1993-03-30 Ciba-Geigy Corporation Process for the preparation of optically active aliphatic hydroxycarboxylic acids
EP0643065A1 (en) * 1993-09-10 1995-03-15 Bayer Ag Novel bisphosphines for asymetric hydrogenation catalysts
EP0901997A1 (en) * 1997-09-05 1999-03-17 Takasago International Corporation Process for producing optically active alcohol compound
EP0965574A2 (en) * 1998-06-19 1999-12-22 Degussa-Hüls Aktiengesellschaft Process for enantioselective hydrogenation

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
GENET J.P. ET AL.: "Enantioselective hydrogenation reactions with a full set of preformed and prepared in situ chiral diphosphine-ruthenium(II) catalysts", TETRAHEDRON: ASYMMETRY, vol. 5, no. 4, 1994, pages 675 - 690, XP002249781, ISSN: 0957-4166 *
OHNO A. ET AL.: "Reduction by a model of NAD(P)H. 25. A chiral model which induces high asymmetry", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 101, no. 23, 1979, pages 7036 - 7040, XP002253904 *
SAITO T. ET AL.: "New chiral diphosphine ligands designed to have a narrow dihedral angle in the biaryl backbone", ADVANCED SYNTHESIS & CATALYSIS, vol. 343, no. 3, 1 March 2001 (2001-03-01), pages 264 - 267, XP002253903 *
SCHUMMER A. ET AL.: "POLYFUNCTIONAL (R)-2-HYDROXYCARBOXYLIC ACIDS BY REDUCTION OF 2-OXO ACIDS WITH HYDROGEN GAS OR FORMATE AND RESTING CELLS OF PROTEUS VULGARIS", TETRAHEDRON, vol. 47, no. 43, 1991, pages 9019 - 9034, XP000196414, ISSN: 0040-4020 *

Also Published As

Publication number Publication date
US20020035271A1 (en) 2002-03-21
DE10027154A1 (en) 2001-12-13
JP2002003441A (en) 2002-01-09
US6583312B2 (en) 2003-06-24
EP1160237A2 (en) 2001-12-05

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